6,7-dimethoxy-1-(4-(trifluoromethyl)phenyl)-1,2,3,4-tetrahydroisoquinoline | 596788-79-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 四氢异喹啉
• 英文名称: 6,7-dimethoxy-1-(4-(trifluoromethyl)phenyl)-1,2,3,4-tetrahydroisoquinoline
• 英文别名: 6,7-Dimethoxy-1-[4-(trifluoromethyl)phenyl]-1,2,3,4-tetrahydroisoquinoline
• CAS: 596788-79-3
• 化学式: C₁₈H₁₈F₃NO₂
• 分子量: 337.342
• InChiKey: AEMIRCPNFVHJCV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  30.5
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  6,7-dimethoxy-1-(4-(trifluoromethyl)phenyl)-1,2,3,4-tetrahydroisoquinoline 在 N,N-二异丙基乙胺 作用下， 以 乙腈 为溶剂， 反应 39.0h， 生成 3-ethyl-8,9-dimethoxy-5-(4-methylphenylsulfonyl)-6-(4-trifluoromethylphenyl)-1,2,3,6-tetrahydrobenzo[d]azocine
  参考文献：
  名称：

  使用活化炔烃串联扩增1-芳基-四氢异喹啉中的四氢吡啶环-一种新的有效合成苯并偶氮化合物

  摘要：

  四氢异喹啉图3a - ë后行哌啶环活化的炔烃的作用下增大，给予benzoazocines 4，5和7 - 11以高收率。

  DOI：

  10.1016/j.tetlet.2006.04.151
• 作为产物：
  描述：

  在 三氟乙酸 作用下， 反应 4.0h， 生成 6,7-dimethoxy-1-(4-(trifluoromethyl)phenyl)-1,2,3,4-tetrahydroisoquinoline
  参考文献：
  名称：

  1-Aryl-tetrahydroisoquinoline analogs as active anti-HIV agents in vitro

  摘要：

  A series of 1-aryl-6,7-dihydroxyl(methoxy)-1,2,3,4-tetrahydroisoquinolines (compounds 1-36) were synthesized via Pictet-Spengler cyclization. All the synthesized compounds were assayed for activities against HIV-1(IIIB) in C8166 cell cultures by MTT method for the first time. The results of the anti-HIV screening revealed that 6,7-dihydroxytetrahydroisoquinolines possessed higher selective index than 6,7-dimethoxyl analogs due to the significantly decreased cytotoxicities. Compounds 6, 24, and 36 showed potent anti-HIV activities with EC50 values of 8.2, 4.6, and 5.3 mu M respectively, and the cytotoxicities (CC50) of these three compounds were 784.3, 727.3, and 687.3 mu M, which resulted in SI values larger than 95, 159, and 130 respectively. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.02.040

文献信息

• Synthesis of Benzoazocines from Substituted Tetrahydroisoquinolines and Activated Alkynes in a Tetrahydropyridine Ring Expansion
  作者：Leonid G. Voskressensky、Anna V. Listratova、Tatiana N. Borisova、Grigoriy G. Alexandrov、Alexey V. Varlamov

  DOI：10.1002/ejoc.200700602

  日期：2007.12

  Tetrahydroisoquinolines underwent tandem piperidine ring enlargement in the presence of activated alkynes in acetonitrile or methanol, producing tetrahydrobenzo[d]azocines in high yields. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)

  四氢异喹啉在乙腈或甲醇中存在活化炔烃的情况下经历串联哌啶环扩大，以高产率生产四氢苯并[d]偶氮辛。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)
• Redox-Annulations of Cyclic Amines with Electron-Deficient <i>o</i>-Tolualdehydes
  作者：Anirudra Paul、Alafate Adili、Daniel Seidel

  DOI：10.1021/acs.orglett.9b00438

  日期：2019.3.15

  Amines such as 1,2,3,4-tetrahydroisoquinoline undergo redox-neutral annulations with 2-methyl-3,5-dinitrobenzaldehyde and closely related substrates. Acetic acid serves as the solvent and sole promoter of these transformations which involve dual C-H functionalization.
• Redox-Annulations of Cyclic Amines with <i>ortho</i>-Cyanomethylbenzaldehydes
  作者：Anirudra Paul、Hemant S. Chandak、Longle Ma、Daniel Seidel

  DOI：10.1021/acs.orglett.9b04506

  日期：2020.2.7

  Amines such as 1,2,3,4-tetrahydroisoquinoline undergo redox-neutral annulations with ortho-cyanomethylbenzaldehydes. These amine alpha-C-H bond functionalization reactions are promoted by acetic acid. The resulting beta-aminonitriles can be converted to the corresponding beta-aminoalcohols in diastereoselective fashion.
• 1-Aryl-tetrahydroisoquinoline analogs as active anti-HIV agents in vitro
  作者：Pi Cheng、Ning Huang、Zhi-Yong Jiang、Quan Zhang、Yong-Tang Zheng、Ji-Jun Chen、Xue-Mei Zhang、Yun-Bao Ma

  DOI：10.1016/j.bmcl.2008.02.040

  日期：2008.4

  A series of 1-aryl-6,7-dihydroxyl(methoxy)-1,2,3,4-tetrahydroisoquinolines (compounds 1-36) were synthesized via Pictet-Spengler cyclization. All the synthesized compounds were assayed for activities against HIV-1(IIIB) in C8166 cell cultures by MTT method for the first time. The results of the anti-HIV screening revealed that 6,7-dihydroxytetrahydroisoquinolines possessed higher selective index than 6,7-dimethoxyl analogs due to the significantly decreased cytotoxicities. Compounds 6, 24, and 36 showed potent anti-HIV activities with EC50 values of 8.2, 4.6, and 5.3 mu M respectively, and the cytotoxicities (CC50) of these three compounds were 784.3, 727.3, and 687.3 mu M, which resulted in SI values larger than 95, 159, and 130 respectively. (C) 2008 Elsevier Ltd. All rights reserved.
• Tandem enlargement of the tetrahydropyridine ring in 1-aryl-tetrahydroisoquinolines using activated alkynes—a new and effective synthesis of benzoazocines
  作者：Leonid G. Voskressensky、Tatiana N. Borisova、Anna V. Listratova、Larisa N. Kulikova、Alexander A. Titov、Alexey V. Varlamov

  DOI：10.1016/j.tetlet.2006.04.151

  日期：2006.7

  Tetrahydroisoquinolines 3a–e underwent piperidine ring enlargement under the action of activated alkynes, giving benzoazocines 4, 5 and 7–11 in high yields.

  四氢异喹啉图3a - ë后行哌啶环活化的炔烃的作用下增大，给予benzoazocines 4，5和7 - 11以高收率。